Triethylamine → Methyl furo[2,3-b]quinoline-4-carboxylate

HRID 641134Notes

Reaction equation

HRID 641134 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]=1[CH:16]=[CH2:17])=[O:4].BrBr.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]2[O:15][CH:17]=[CH:16][C:6]=12)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 12294102Methyl-2-oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylate

Product 1

HCID 70902591Methyl furo[2,3-b]quinoline-4-carboxylateYield 43.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2.6 g (11.2 mmol) Methyl-2-oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylate 5 in 200 mL chloroform was added slowly over a dropping funnel a solution of 2.16 g (13.5 mmol) bromine in 15 mL chloroform and subsequently 6.8 mL of triethylamine. The reaction mixture was heated at reflux for 4.5 hour. After evaporation of the solvent the residue was purified by column chromatography on silica gel, eluting with toluene/ethyl acetate/methanol 4:1:1, to give 1.1 g of the desired product 6.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4.5 hour
  3. customAfter evaporation of the solvent the residue
  4. customwas purified by column chromatography on silica gel
  5. washeluting with toluene/ethyl acetate/methanol 4:1:1

Sources & evidence

ORD record
ord-f6aa2db418af4b91b2185af48162bdc6
Source dataset
uspto-grants-2010_04
Patent number
US07695980B2

Reaction notes

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